Glycoside compound, method for producing thioether, ether, method for producing ether, method for producing glycoside compound, method for producing nucleic acid

Abstract

The invention provides a glucoside compound, which is capable of providing a phosphoramidite, which can be produced at low cost and can produce a nucleic acid in high yield and with high purity. The glycoside compound has the formula wherein B, R1, R2, and R3 are as described herein.

The invention claimed is: 
     
       1. An ether represented by the following chemical formula (106): 
       
         
           
           
               
               
           
         
         in the aforementioned chemical formula (106), 
         R 4  is a hydrocarbon group, a straight chain or branched alkyl group, a straight chain or branched alkenyl group, a straight chain or branched alkynyl group, an aryl group, a straight chain or branched arylalkyl group, a cycloalkyl group, a cycloalkenyl group, a straight chain or branched cycloalkylalkyl group, a straight chain or branched cyclylalkyl group, or a straight chain or branched alkoxyalkyl group, 
         n is a positive integer, 
         L 1  is an ethylene group (—CH 2 CH 2 —), wherein hydrogen atoms besides a hydrogen atom bonded to the α-position relative to [D 1 ] are optionally substituted by a straight chain or branched alkyl group, and 
         [D 1 ] is an electron-withdrawing group, 
       
       an enantiomer thereof, a tautomer or stereoisomer thereof or a salt thereof. 
     
     
       2. A method of producing the ether according to  claim 1 , comprising a coupling reaction of a thioether represented by the following chemical formula (103) and an alcohol represented by the following chemical formula (105), in the presence of a halogenating agent and a Lewis acid, 
       
         
           
           
               
               
           
         
         in the aforementioned chemical formulas (103) and (105), 
         R 4  is as defined for the aforementioned chemical formula (106), 
         R 5  is a hydrocarbon group, a straight chain or branched alkyl group, a straight chain or branched alkenyl group, a straight chain or branched alkynyl group, an aryl group, a straight chain or branched arylalkyl group, a cycloalkyl group, a cycloalkenyl group, a straight chain or branched cycloalkylalkyl group, a straight chain or branched cyclylalkyl group, or a straight chain or branched alkoxyalkyl group, which may be the same as or different from R 4 , 
         in the aforementioned chemical formula (103), 
         n is as defined for the aforementioned chemical formula (106), and 
         in the aforementioned chemical formula (105), 
         L 1  and [D 1 ] are as defined for the aforementioned chemical formula (106). 
       
     
     
       3. The production method according to  claim 2 , wherein the aforementioned halogenating agent is at least one selected from the group consisting of N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, iodine, bromine and chlorine. 
     
     
       4. The production method according to  claim 2 , wherein the aforementioned Lewis acid is at least one selected from the group consisting of perfluoroalkylcarboxylic acid, perfluoroalkylsulfonic acid, alkylsulfonic acid and a salt thereof. 
     
     
       5. The production method according to  claim 2 , wherein the aforementioned Lewis acid is a silver salt of trifluoromethanesulfonic acid. 
     
     
       6. The production method according to  claim 2 , wherein the aforementioned coupling reaction is performed in the co-presence of molecular sieve. 
     
     
       7. The production method according to  claim 6 , further comprising a step of producing the thioether represented by the chemical formula (103) by the production method comprising a coupling reaction of thiol or thioalkoxide represented by the chemical formulas (101a) and (101b) with a halide represented by the chemical formula (102) to give a thioether represented by the chemical formula (103): 
       
         
           
           
               
               
           
         
       
       wherein
 in the aforementioned chemical formulas (101a), (101b) and (103), 
 R 4  and R 5  are each a hydrocarbon group, a straight chain or branched alkyl group, a straight chain or branched alkenyl group, a straight chain or branched alkynyl group, an aryl group, a straight chain or branched arylalkyl group, a cycloalkyl group, a cycloalkenyl group, a straight chain or branched cycloalkylalkyl group, a straight chain or branched cyclylalkyl group, or a straight chain or branched alkoxyalkyl group, which may be the same or different, 
 in the aforementioned chemical formulas (101a) and (101b), 
 M 1  and M 2  may be the same or different and each is a hydrogen atom or a metal, 
 in the aforementioned chemical formulas (102) and (103), 
 n is a positive integer, and 
 in the aforementioned chemical formula (102), 
 X 1  and X 2  may be the same or different and each is halogen. 
 
     
     
       8. The production method according to  claim 7 , wherein, in the aforementioned chemical formulas (101a), (101b) and (103), R 4  and R 5  are each a methyl group.